#------------------------------------------------------------------------------
#$Date: 2008-01-14 00:15:36 +0200 (Mon, 14 Jan 2008) $
#$Revision: 14 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013873.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_2013873
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2004
_journal_volume  60
_journal_page_first  o191
_journal_page_last  o193
_publ_section_title
;
4-Amino-1-methyl-5-(2-hydroxy-4,4-dimethyl-2-oxocyclohexenylmethyl)-
2-(methylsulfanyl)pyrimidin-6(1H)-one:
hydrogen-bonded chains are \p-stacked in pairs
;
loop_
_publ_author_name
  'Low, John N.'
  'Cobo, Justo'
  'Cruz, Silvia'
  'Quiroga, Jairo'
  'Glidewell, Christopher'
_chemical_formula_moiety  'C15 H21 N3 O3 S'
_chemical_formula_sum  'C15 H21 N3 O3 S'
_chemical_formula_iupac  'C15 H21 N3 O3 S'
_chemical_formula_weight  323.41
_symmetry_cell_setting  monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x+1/2, -y+1/2, z+1/2'
_cell_length_a  7.5524(2)
_cell_length_b  7.1370(3)
_cell_length_c  28.6208(11)
_cell_angle_alpha  90.00
_cell_angle_beta  93.128(2)
_cell_angle_gamma  90.00
_cell_volume  1540.40(10)
_cell_formula_units_Z  4
_cell_measurement_temperature  120(2)
_exptl_crystal_density_diffrn  1.394
_diffrn_ambient_temperature  120(2)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
  N1 0.7539(2) 0.3798(2) 0.49141(5) 0.0198(3) Uani d . 1 . . N
  C2 0.7498(2) 0.5505(3) 0.51029(6) 0.0194(4) Uani d . 1 . . C
  N3 0.6955(2) 0.6963(2) 0.48764(5) 0.0213(3) Uani d . 1 . . N
  C4 0.6362(2) 0.6744(2) 0.44168(6) 0.0200(4) Uani d . 1 . . C
  N4 0.5820(2) 0.8288(2) 0.41993(5) 0.0255(4) Uani d . 1 . . N
  C5 0.6339(2) 0.5062(2) 0.41944(6) 0.0194(4) Uani d . 1 . . C
  C6 0.7005(2) 0.3536(3) 0.44411(6) 0.0208(4) Uani d . 1 . . C
  O6 0.71906(19) 0.19762(17) 0.42643(4) 0.0262(3) Uani d . 1 . . O
  C11 0.8209(3) 0.2222(3) 0.51881(7) 0.0260(4) Uani d . 1 . . C
  S2 0.82976(6) 0.56773(7) 0.568820(15) 0.02358(14) Uani d . 1 . . S
  C21 0.7849(3) 0.8037(3) 0.57990(7) 0.0307(5) Uani d . 1 . . C
  C57 0.5750(2) 0.4850(3) 0.36838(6) 0.0206(4) Uani d . 1 . . C
  C51 0.7154(2) 0.5431(3) 0.33565(6) 0.0191(4) Uani d . 1 . . C
  C52 0.8609(2) 0.4398(2) 0.32941(6) 0.0198(4) Uani d . 1 . . C
  O52 0.88973(18) 0.27490(17) 0.34900(4) 0.0238(3) Uani d . 1 . . O
  C53 1.0093(2) 0.4934(3) 0.29979(6) 0.0217(4) Uani d . 1 . . C
  C54 1.0156(2) 0.6982(3) 0.28889(6) 0.0226(4) Uani d . 1 . . C
  C55 0.8268(2) 0.7601(3) 0.27475(6) 0.0229(4) Uani d . 1 . . C
  C56 0.6944(2) 0.7138(3) 0.31032(6) 0.0211(4) Uani d . 1 . . C
  O56 0.5690(2) 0.8186(2) 0.31668(6) 0.0277(4) Uani d . 1 . . O
  C541 1.0852(3) 0.8074(3) 0.33172(7) 0.0297(4) Uani d . 1 . . C
  C542 1.1342(3) 0.7320(3) 0.24834(8) 0.0325(5) Uani d . 1 . . C
  H11A 0.7994 0.1061 0.5011 0.039 Uiso calc R 1 . . H
  H11B 0.7602 0.2160 0.5482 0.039 Uiso calc R 1 . . H
  H11C 0.9486 0.2376 0.5257 0.039 Uiso calc R 1 . . H
  H21A 0.8014 0.8281 0.6136 0.046 Uiso calc R 1 . . H
  H21B 0.6623 0.8323 0.5693 0.046 Uiso calc R 1 . . H
  H21C 0.8660 0.8829 0.5630 0.046 Uiso calc R 1 . . H
  H4A 0.5433 0.8241 0.3904 0.031 Uiso calc R 1 . . H
  H4B 0.5845 0.9364 0.4350 0.031 Uiso calc R 1 . . H
  H57A 0.5428 0.3525 0.3622 0.025 Uiso calc R 1 . . H
  H57B 0.4675 0.5620 0.3617 0.025 Uiso calc R 1 . . H
  H52 0.8159 0.2569 0.3695 0.036 Uiso calc R 1 . . H
  H53A 0.9975 0.4225 0.2701 0.026 Uiso calc R 1 . . H
  H53B 1.1229 0.4564 0.3161 0.026 Uiso calc R 1 . . H
  H54A 1.0781 0.9420 0.3251 0.044 Uiso calc R 1 . . H
  H54B 1.2089 0.7725 0.3394 0.044 Uiso calc R 1 . . H
  H54C 1.0134 0.7780 0.3583 0.044 Uiso calc R 1 . . H
  H54G 1.1285 0.8644 0.2393 0.049 Uiso calc R 1 . . H
  H54H 1.0936 0.6543 0.2216 0.049 Uiso calc R 1 . . H
  H54I 1.2568 0.6989 0.2580 0.049 Uiso calc R 1 . . H
  H55A 0.8263 0.8972 0.2695 0.027 Uiso calc R 1 . . H
  H55B 0.7894 0.6992 0.2447 0.027 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
  N1 0.0252(8) 0.0148(7) 0.0195(7) 0.0005(6) 0.0023(6) 0.0021(6)
  C2 0.0188(9) 0.0199(9) 0.0198(8) -0.0010(7) 0.0037(7) 0.0001(7)
  N3 0.0263(8) 0.0177(8) 0.0197(7) 0.0002(6) 0.0005(6) 0.0009(6)
  C4 0.0209(9) 0.0184(9) 0.0207(9) 0.0000(7) 0.0026(7) 0.0020(7)
  N4 0.0377(10) 0.0171(8) 0.0211(8) 0.0043(7) -0.0038(7) -0.0001(6)
  C5 0.0222(9) 0.0174(9) 0.0188(8) -0.0026(7) 0.0025(7) 0.0003(7)
  C6 0.0243(10) 0.0185(10) 0.0200(9) -0.0034(7) 0.0057(7) 0.0010(7)
  O6 0.0401(8) 0.0141(7) 0.0243(7) -0.0012(6) 0.0027(6) 0.0004(5)
  C11 0.0349(11) 0.0189(10) 0.0241(9) 0.0032(8) 0.0019(8) 0.0045(7)
  S2 0.0294(3) 0.0223(3) 0.0187(2) 0.0011(2) -0.00129(17) 0.00093(18)
  C21 0.0402(12) 0.0274(11) 0.0236(10) 0.0053(9) -0.0058(8) -0.0036(8)
  C57 0.0234(9) 0.0186(9) 0.0198(9) -0.0014(7) 0.0009(7) 0.0002(7)
  C51 0.0209(9) 0.0201(9) 0.0160(8) -0.0010(7) -0.0015(7) -0.0001(7)
  C52 0.0276(10) 0.0156(9) 0.0157(8) -0.0016(7) -0.0023(7) -0.0016(7)
  O52 0.0325(8) 0.0161(7) 0.0231(7) 0.0029(6) 0.0045(5) 0.0023(5)
  C53 0.0254(10) 0.0204(9) 0.0194(9) 0.0014(8) 0.0014(7) -0.0003(7)
  C54 0.0236(10) 0.0205(10) 0.0238(9) -0.0012(8) 0.0014(7) 0.0011(7)
  C55 0.0272(10) 0.0198(9) 0.0215(9) -0.0010(8) 0.0000(7) 0.0036(7)
  C56 0.0233(10) 0.0218(10) 0.0178(8) 0.0002(8) -0.0032(7) -0.0007(7)
  O56 0.0291(7) 0.0261(7) 0.0273(7) 0.0080(6) 0.0029(6) 0.0057(6)
  C541 0.0291(11) 0.0234(10) 0.0359(11) -0.0024(8) -0.0041(8) -0.0036(9)
  C542 0.0311(11) 0.0297(11) 0.0376(11) -0.0017(9) 0.0095(9) 0.0061(9)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  N1 C2 . 1.334(2) y
  C2 N3 . 1.282(2) y
  N3 C4 . 1.375(2) y
  C4 C5 . 1.359(3) y
  C5 C6 . 1.378(3) y
  C6 N1 . 1.404(2) y
  C2 S2 . 1.7536(18) y
  S2 C21 . 1.750(2) y
  N1 C11 . 1.447(2) y
  C4 N4 . 1.319(2) y
  C6 O6 . 1.234(2) y
  C51 C52 . 1.343(3) y
  C52 O52 . 1.317(2) y
  C51 C56 . 1.423(3) y
  C56 O56 . 1.227(2) y
  C11 H11A . 0.98 no
  C11 H11B . 0.98 no
  C11 H11C . 0.98 no
  C21 H21A . 0.98 no
  C21 H21B . 0.98 no
  C21 H21C . 0.98 no
  N4 H4A . 0.88 no
  N4 H4B . 0.88 no
  C5 C57 . 1.512(2) no
  C57 C51 . 1.511(2) no
  C57 H57A . 0.99 no
  C57 H57B . 0.99 no
  C52 C53 . 1.491(3) no
  O52 H52 . 0.84 no
  C53 C54 . 1.496(3) no
  C53 H53A . 0.99 no
  C53 H53B . 0.99 no
  C54 C541 . 1.522(3) no
  C54 C542 . 1.523(3) no
  C54 C55 . 1.526(3) no
  C541 H54A . 0.98 no
  C541 H54B . 0.98 no
  C541 H54C . 0.98 no
  C542 H54G . 0.98 no
  C542 H54H . 0.98 no
  C542 H54I . 0.98 no
  C55 C56 . 1.503(3) no
  C55 H55A . 0.99 no
  C55 H55B . 0.99 no